EP2454333A1 - An aqueous ink jet ink comprising a crosslinking pigment dispersion based on diblock polymeric dispersants - Google Patents
An aqueous ink jet ink comprising a crosslinking pigment dispersion based on diblock polymeric dispersantsInfo
- Publication number
- EP2454333A1 EP2454333A1 EP10732617A EP10732617A EP2454333A1 EP 2454333 A1 EP2454333 A1 EP 2454333A1 EP 10732617 A EP10732617 A EP 10732617A EP 10732617 A EP10732617 A EP 10732617A EP 2454333 A1 EP2454333 A1 EP 2454333A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- block
- ink jet
- methacrylate
- group
- aqueous
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000006185 dispersion Substances 0.000 title claims abstract description 122
- 239000002270 dispersing agent Substances 0.000 title claims abstract description 91
- 239000000049 pigment Substances 0.000 title claims description 129
- 238000004132 cross linking Methods 0.000 title description 36
- 239000000178 monomer Substances 0.000 claims abstract description 77
- 239000002245 particle Substances 0.000 claims abstract description 51
- 239000007787 solid Substances 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 229920001400 block copolymer Polymers 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 10
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910000077 silane Inorganic materials 0.000 claims abstract description 8
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001718 carbodiimides Chemical class 0.000 claims abstract description 7
- 239000012948 isocyanate Substances 0.000 claims abstract description 7
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 7
- 239000003431 cross linking reagent Substances 0.000 claims abstract description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
- 229920000642 polymer Polymers 0.000 claims description 41
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 34
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 30
- -1 lauryl ethacrylate Chemical compound 0.000 claims description 23
- 239000000203 mixture Substances 0.000 claims description 22
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 17
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 125000003118 aryl group Chemical group 0.000 claims description 10
- AOJOEFVRHOZDFN-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate Chemical group CC(=C)C(=O)OCC1=CC=CC=C1 AOJOEFVRHOZDFN-UHFFFAOYSA-N 0.000 claims description 8
- 239000003086 colorant Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 6
- 150000002924 oxiranes Chemical class 0.000 claims description 6
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 claims description 5
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 4
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000129 anionic group Chemical group 0.000 claims description 4
- 125000002091 cationic group Chemical group 0.000 claims description 4
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 claims description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 239000011976 maleic acid Substances 0.000 claims description 4
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 claims description 4
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 claims description 4
- 229920002554 vinyl polymer Polymers 0.000 claims description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims description 3
- RBFPEAGEJJSYCX-UHFFFAOYSA-N 2-[2-(2-ethoxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical group CCOCCOCCOCCOC(=O)C(C)=C RBFPEAGEJJSYCX-UHFFFAOYSA-N 0.000 claims description 3
- DJKKWVGWYCKUFC-UHFFFAOYSA-N 2-butoxyethyl 2-methylprop-2-enoate Chemical compound CCCCOCCOC(=O)C(C)=C DJKKWVGWYCKUFC-UHFFFAOYSA-N 0.000 claims description 3
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 claims description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 3
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical compound OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 claims description 3
- 239000000945 filler Substances 0.000 claims description 3
- 239000013528 metallic particle Substances 0.000 claims description 3
- AOUAMFARIYTDLK-UHFFFAOYSA-N (4-methylphenyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=C(C)C=C1 AOUAMFARIYTDLK-UHFFFAOYSA-N 0.000 claims description 2
- OJNXPAPLAAGFBJ-UHFFFAOYSA-N (4-methylphenyl) prop-2-enoate Chemical compound CC1=CC=C(OC(=O)C=C)C=C1 OJNXPAPLAAGFBJ-UHFFFAOYSA-N 0.000 claims description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 claims description 2
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 claims description 2
- AIIITCMZOKMJIM-UHFFFAOYSA-N 2-(prop-2-enoylamino)propane-2-sulfonic acid Chemical compound OS(=O)(=O)C(C)(C)NC(=O)C=C AIIITCMZOKMJIM-UHFFFAOYSA-N 0.000 claims description 2
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 claims description 2
- KDAKDBASXBEFFK-UHFFFAOYSA-N 2-(tert-butylamino)ethyl prop-2-enoate Chemical compound CC(C)(C)NCCOC(=O)C=C KDAKDBASXBEFFK-UHFFFAOYSA-N 0.000 claims description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 2
- CEXQWAAGPPNOQF-UHFFFAOYSA-N 2-phenoxyethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC1=CC=CC=C1 CEXQWAAGPPNOQF-UHFFFAOYSA-N 0.000 claims description 2
- JTHZUSWLNCPZLX-UHFFFAOYSA-N 6-fluoro-3-methyl-2h-indazole Chemical compound FC1=CC=C2C(C)=NNC2=C1 JTHZUSWLNCPZLX-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 claims description 2
- GYCMBHHDWRMZGG-UHFFFAOYSA-N Methylacrylonitrile Chemical compound CC(=C)C#N GYCMBHHDWRMZGG-UHFFFAOYSA-N 0.000 claims description 2
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 claims description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 claims description 2
- 229960003237 betaine Drugs 0.000 claims description 2
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- AEDZKIACDBYJLQ-UHFFFAOYSA-N ethane-1,2-diol;hydrate Chemical compound O.OCCO AEDZKIACDBYJLQ-UHFFFAOYSA-N 0.000 claims description 2
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 claims description 2
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims description 2
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- PBOSTUDLECTMNL-UHFFFAOYSA-N lauryl acrylate Chemical compound CCCCCCCCCCCCOC(=O)C=C PBOSTUDLECTMNL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000787 lecithin Substances 0.000 claims description 2
- 229940067606 lecithin Drugs 0.000 claims description 2
- 235000010445 lecithin Nutrition 0.000 claims description 2
- HMZGPNHSPWNGEP-UHFFFAOYSA-N octadecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C(C)=C HMZGPNHSPWNGEP-UHFFFAOYSA-N 0.000 claims description 2
- NZIDBRBFGPQCRY-UHFFFAOYSA-N octyl 2-methylprop-2-enoate Chemical compound CCCCCCCCOC(=O)C(C)=C NZIDBRBFGPQCRY-UHFFFAOYSA-N 0.000 claims description 2
- 229940065472 octyl acrylate Drugs 0.000 claims description 2
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 claims description 2
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 claims description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 claims description 2
- QIWKUEJZZCOPFV-UHFFFAOYSA-N phenyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1=CC=CC=C1 QIWKUEJZZCOPFV-UHFFFAOYSA-N 0.000 claims description 2
- WRAQQYDMVSCOTE-UHFFFAOYSA-N phenyl prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1 WRAQQYDMVSCOTE-UHFFFAOYSA-N 0.000 claims description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 2
- 239000010452 phosphate Substances 0.000 claims description 2
- NHARPDSAXCBDDR-UHFFFAOYSA-N propyl 2-methylprop-2-enoate Chemical compound CCCOC(=O)C(C)=C NHARPDSAXCBDDR-UHFFFAOYSA-N 0.000 claims description 2
- PNXMTCDJUBJHQJ-UHFFFAOYSA-N propyl prop-2-enoate Chemical compound CCCOC(=O)C=C PNXMTCDJUBJHQJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000003440 styrenes Chemical class 0.000 claims description 2
- 150000003871 sulfonates Chemical class 0.000 claims description 2
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims 1
- 125000001165 hydrophobic group Chemical group 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 230000003287 optical effect Effects 0.000 abstract description 4
- 150000002118 epoxides Chemical class 0.000 abstract 1
- 239000000976 ink Substances 0.000 description 114
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 238000000034 method Methods 0.000 description 34
- 239000003981 vehicle Substances 0.000 description 34
- 238000003801 milling Methods 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
- 230000008569 process Effects 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Substances [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 18
- 239000004615 ingredient Substances 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002156 mixing Methods 0.000 description 14
- 239000003054 catalyst Substances 0.000 description 13
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 230000006641 stabilisation Effects 0.000 description 11
- 238000011105 stabilization Methods 0.000 description 11
- ZSPOJBDHHFFJAP-UHFFFAOYSA-M 3-chlorobenzoate;tetrabutylazanium Chemical compound [O-]C(=O)C1=CC=CC(Cl)=C1.CCCC[N+](CCCC)(CCCC)CCCC ZSPOJBDHHFFJAP-UHFFFAOYSA-M 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 238000011068 loading method Methods 0.000 description 10
- 238000001035 drying Methods 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 8
- 239000008367 deionised water Substances 0.000 description 7
- 238000005227 gel permeation chromatography Methods 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 7
- 239000000758 substrate Substances 0.000 description 7
- 239000006229 carbon black Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 238000007641 inkjet printing Methods 0.000 description 6
- 238000007639 printing Methods 0.000 description 6
- 239000008135 aqueous vehicle Substances 0.000 description 5
- 239000006227 byproduct Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 239000003999 initiator Substances 0.000 description 5
- 230000000704 physical effect Effects 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000010926 purge Methods 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- PGQNYIRJCLTTOJ-UHFFFAOYSA-N trimethylsilyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)O[Si](C)(C)C PGQNYIRJCLTTOJ-UHFFFAOYSA-N 0.000 description 5
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 230000032683 aging Effects 0.000 description 4
- 238000005189 flocculation Methods 0.000 description 4
- 230000016615 flocculation Effects 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000012860 organic pigment Substances 0.000 description 4
- 229920000573 polyethylene Polymers 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000003643 water by type Substances 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000006184 cosolvent Substances 0.000 description 3
- 229910003460 diamond Inorganic materials 0.000 description 3
- 239000010432 diamond Substances 0.000 description 3
- 150000002334 glycols Chemical class 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 239000001023 inorganic pigment Substances 0.000 description 3
- 238000006386 neutralization reaction Methods 0.000 description 3
- 125000006353 oxyethylene group Chemical group 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 229910001220 stainless steel Inorganic materials 0.000 description 3
- 239000010935 stainless steel Substances 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004873 anchoring Methods 0.000 description 2
- 239000008365 aqueous carrier Substances 0.000 description 2
- QXJJQWWVWRCVQT-UHFFFAOYSA-K calcium;sodium;phosphate Chemical compound [Na+].[Ca+2].[O-]P([O-])([O-])=O QXJJQWWVWRCVQT-UHFFFAOYSA-K 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000000356 contaminant Substances 0.000 description 2
- 238000011109 contamination Methods 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 229920006037 cross link polymer Polymers 0.000 description 2
- 239000012975 dibutyltin dilaurate Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000002296 dynamic light scattering Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
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- 150000002500 ions Chemical class 0.000 description 2
- YIXJRHPUWRPCBB-UHFFFAOYSA-N magnesium nitrate Chemical compound [Mg+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O YIXJRHPUWRPCBB-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 239000003002 pH adjusting agent Substances 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 229920000223 polyglycerol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 2
- 235000013772 propylene glycol Nutrition 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 238000000518 rheometry Methods 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000012430 stability testing Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 1
- 229940015975 1,2-hexanediol Drugs 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- XFOYMWPSASGDSQ-UHFFFAOYSA-N 1-[2-(2-hydroxyethoxy)ethoxy]butan-2-ol;2-methylprop-2-enoic acid Chemical compound CC(=C)C(O)=O.CCC(O)COCCOCCO XFOYMWPSASGDSQ-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- FENFUOGYJVOCRY-UHFFFAOYSA-N 1-propoxypropan-2-ol Chemical compound CCCOCC(C)O FENFUOGYJVOCRY-UHFFFAOYSA-N 0.000 description 1
- GQCZPFJGIXHZMB-UHFFFAOYSA-N 1-tert-Butoxy-2-propanol Chemical compound CC(O)COC(C)(C)C GQCZPFJGIXHZMB-UHFFFAOYSA-N 0.000 description 1
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 description 1
- HRWADRITRNUCIY-UHFFFAOYSA-N 2-(2-propan-2-yloxyethoxy)ethanol Chemical compound CC(C)OCCOCCO HRWADRITRNUCIY-UHFFFAOYSA-N 0.000 description 1
- HUFRRBHGGJPNGG-UHFFFAOYSA-N 2-(2-propan-2-yloxypropoxy)propan-1-ol Chemical compound CC(C)OC(C)COC(C)CO HUFRRBHGGJPNGG-UHFFFAOYSA-N 0.000 description 1
- DJCYDDALXPHSHR-UHFFFAOYSA-N 2-(2-propoxyethoxy)ethanol Chemical compound CCCOCCOCCO DJCYDDALXPHSHR-UHFFFAOYSA-N 0.000 description 1
- XYVAYAJYLWYJJN-UHFFFAOYSA-N 2-(2-propoxypropoxy)propan-1-ol Chemical compound CCCOC(C)COC(C)CO XYVAYAJYLWYJJN-UHFFFAOYSA-N 0.000 description 1
- SJIXRGNQPBQWMK-UHFFFAOYSA-N 2-(diethylamino)ethyl 2-methylprop-2-enoate Chemical compound CCN(CC)CCOC(=O)C(C)=C SJIXRGNQPBQWMK-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- BDLXTDLGTWNUFM-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]ethanol Chemical compound CC(C)(C)OCCO BDLXTDLGTWNUFM-UHFFFAOYSA-N 0.000 description 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- GICQWELXXKHZIN-UHFFFAOYSA-N 2-[2-[(2-methylpropan-2-yl)oxy]ethoxy]ethanol Chemical compound CC(C)(C)OCCOCCO GICQWELXXKHZIN-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- GMWUGZRYXRJLCX-UHFFFAOYSA-N 2-methoxypentan-2-ol Chemical compound CCCC(C)(O)OC GMWUGZRYXRJLCX-UHFFFAOYSA-N 0.000 description 1
- IXPWKHNDQICVPZ-UHFFFAOYSA-N 2-methylhex-1-en-3-yne Chemical compound CCC#CC(C)=C IXPWKHNDQICVPZ-UHFFFAOYSA-N 0.000 description 1
- HCGFUIQPSOCUHI-UHFFFAOYSA-N 2-propan-2-yloxyethanol Chemical compound CC(C)OCCO HCGFUIQPSOCUHI-UHFFFAOYSA-N 0.000 description 1
- NECRQCBKTGZNMH-UHFFFAOYSA-N 3,5-dimethylhex-1-yn-3-ol Chemical class CC(C)CC(C)(O)C#C NECRQCBKTGZNMH-UHFFFAOYSA-N 0.000 description 1
- NTKBNCABAMQDIG-UHFFFAOYSA-N 3-butoxypropan-1-ol Chemical compound CCCCOCCCO NTKBNCABAMQDIG-UHFFFAOYSA-N 0.000 description 1
- GBSGXZBOFKJGMG-UHFFFAOYSA-N 3-propan-2-yloxypropan-1-ol Chemical compound CC(C)OCCCO GBSGXZBOFKJGMG-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical class CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- 230000005653 Brownian motion process Effects 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- FHNINJWBTRXEBC-UHFFFAOYSA-N Sudan III Chemical compound OC1=CC=C2C=CC=CC2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 FHNINJWBTRXEBC-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- ZUQAPLKKNAQJAU-UHFFFAOYSA-N acetylenediol Chemical class OC#CO ZUQAPLKKNAQJAU-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- BEHACUVDSXWNGX-UHFFFAOYSA-N benzyl 2-methylprop-2-enoate;styrene Chemical class C=CC1=CC=CC=C1.CC(=C)C(=O)OCC1=CC=CC=C1 BEHACUVDSXWNGX-UHFFFAOYSA-N 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000005537 brownian motion Methods 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229960002713 calcium chloride Drugs 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 238000011088 calibration curve Methods 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical group COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- VFFDVELHRCMPLY-UHFFFAOYSA-N dimethyldodecyl amine Natural products CC(C)CCCCCCCCCCCN VFFDVELHRCMPLY-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- VPWFPZBFBFHIIL-UHFFFAOYSA-L disodium 4-[(4-methyl-2-sulfophenyl)diazenyl]-3-oxidonaphthalene-2-carboxylate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)C1=CC(C)=CC=C1N=NC1=C(O)C(C([O-])=O)=CC2=CC=CC=C12 VPWFPZBFBFHIIL-UHFFFAOYSA-L 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 238000013467 fragmentation Methods 0.000 description 1
- 238000006062 fragmentation reaction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229920001002 functional polymer Polymers 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- FHKSXSQHXQEMOK-UHFFFAOYSA-N hexane-1,2-diol Chemical compound CCCCC(O)CO FHKSXSQHXQEMOK-UHFFFAOYSA-N 0.000 description 1
- 229940051250 hexylene glycol Drugs 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 235000019239 indanthrene blue RS Nutrition 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- AUHZEENZYGFFBQ-UHFFFAOYSA-N mesitylene Substances CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 1
- 125000001827 mesitylenyl group Chemical group [H]C1=C(C(*)=C(C([H])=C1C([H])([H])[H])C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000010979 pH adjustment Methods 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000001935 peptisation Methods 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000007342 radical addition reaction Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- YODZTKMDCQEPHD-UHFFFAOYSA-N thiodiglycol Chemical compound OCCSCCO YODZTKMDCQEPHD-UHFFFAOYSA-N 0.000 description 1
- 229950006389 thiodiglycol Drugs 0.000 description 1
- 238000006276 transfer reaction Methods 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- NLVXSWCKKBEXTG-UHFFFAOYSA-N vinylsulfonic acid Chemical compound OS(=O)(=O)C=C NLVXSWCKKBEXTG-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
- C09D11/32—Inkjet printing inks characterised by colouring agents
- C09D11/324—Inkjet printing inks characterised by colouring agents containing carbon black
- C09D11/326—Inkjet printing inks characterised by colouring agents containing carbon black characterised by the pigment dispersant
Definitions
- This disclosure relates to novel, stable aqueous dispersions of solid particles, the crosslinked polymeric dispersants that produce the stable aqueous particle dispersions, the process of making the same and the use thereof in ink jet inks.
- These dispersants enable a unique combination of ionic and steric stabilization. In water, they provide only ionic stabilization with a random ionic block, but with the addition of ink vehicle components, these dispersants facilitate entropic repulsion and steric stabilization with an ink vehicle soluble block.
- these dispersants comprising crosslinkable moieties are crosslinked with a crosslinking compound such that the particles are dispersed in a crosslinked polymer matrix.
- Aqueous dispersions of solid particles are known in the art and have been used in various applications such as, for example, inks for printing (particularly ink jet printing); waterborne paints and other coating formulations for vehicles, buildings, road markings and the like; cosmetics; pharmaceutical preparations; etc.
- pigment particles are typically not soluble in an aqueous ink vehicle; it is often required to use dispersing agents, such as polymeric dispersants or surfactants, to produce a stable dispersion of the pigment in the ink vehicle.
- An application of the present disclosure relates to an ink (printing liquid) useful for writing utensils such as aqueous ball point pens, fountain pens and felt-tip pens; continuous and on-demand type inkjet printers of a thermal jet type, a piezo type and the like; and an inkjet printing method employing the ink.
- ink printing liquid
- Aqueous particle dispersions generally are stabilized by either a non-ionic or ionic technique.
- a non-ionic technique When the non-ionic technique is used, a polymer having a non-ionic hydrophilic section that extends into the water medium is typically employed.
- the hydrophilic section provides entropic or steric stabilization that stabilizes the solid particles in the aqueous ink vehicle.
- Polyvinyl alcohol, cellulosics, ethylene oxide modified phenols and ethylene oxide/propylene oxide polymers may be used for this purpose.
- non-ionic technique is not sensitive to pH changes or ionic contamination, it has a major disadvantage in that the printed image is water sensitive. Thus, non-ionic content should be minimized to ensure durability.
- the solid particles are stabilized using the polymer of an ion containing monomer, such as neutralized acrylic, maleic or vinyl sulfonic acid.
- the polymer provides stabilization through a charged double layer mechanism whereby ionic repulsion hinders the particles from flocculation. Since the neutralizing component tends to evaporate after printing, the polymer then has reduced water solubility and the printed image is not water sensitive.
- the disclosure provides an aqueous ink jet ink comprising an ink vehicle and an aqueous dispersion, wherein the aqueous dispersion comprises a solid particle and a polymeric dispersant that has been crosslinked, wherein the polymeric dispersant is a block copolymer comprising an A block and a B block, wherein the A block is a segment having a block size of about 5 to about 18 units, and comprises at least 50% by weight of a monomer, having the following structure:
- R and Ri are H, or methyl
- R 2 is alkyl of 1 -4 carbon atoms or phenyl
- n is about 1 about 20;
- the B block is a segment comprising an ionic monomer and at least one hydrophobic monomer; and wherein the dispersant comprises a
- crosslinkable moiety wherein the crosslinkable moiety is crosslinked with a crosslinking agent selected from the group consisting of epoxide, carbodiimide, oxazoline, isocyanate, and silane; and wherein the aqueous dispersion has a pH of at least about 8.0, more typically about 8.0 to about 12.0, and most typically about 8.0 to about 11.0.
- a crosslinking agent selected from the group consisting of epoxide, carbodiimide, oxazoline, isocyanate, and silane
- the solid particle is selected from the group consisting of a colorant such as pigment or insoluble dye, fillers such as silica, metallic particles, biologically active compounds, pharmaceutically active compounds, polymer particles and hollow glass spheres.
- a colorant such as pigment or insoluble dye
- fillers such as silica, metallic particles, biologically active compounds, pharmaceutically active compounds, polymer particles and hollow glass spheres.
- the aqueous dispersions of this disclosure comprise a solid particle and a crosslinked polymeric dispersant. Further the ink jet inks comprise an ink vehicle and the aqueous dispersions. These inks provide images with the requisite stability, optical density and chroma needed for emerging ink jet applications.
- Aqueous Dispersions :
- the type and composition of the solid particle is not particularly critical and will largely depend upon the ultimate end use application of the aqueous dispersion.
- the solid particle is at least substantially insoluble in the liquid vehicle, typically water.
- the solid particle may be organic, inorganic or mixtures thereof.
- suitable solid particles include colorants such as pigments and insoluble dyes, fillers such as silica, metallic particles, biologically active compounds, pharmaceutically active compounds, polymer particles, hollow glass spheres, etc.
- pigments may be selected to make the aqueous dispersion and ink jet ink.
- the term "pigment” as used herein means an insoluble colorant.
- the pigment particles are sufficiently small to permit free flow of the ink through the ink jet printing device, especially at the ejecting nozzles that usually have a diameter ranging from about 10 micron to about 50 micron.
- the particle size also has an influence on the aqueous dispersion stability, which is critical throughout the life of the ink jet ink. Brownian motion of minute particles will help prevent the particles from flocculation. It is also desirable to use small particles for maximum color strength and gloss.
- the range of useful particle sizes is typically about 0.005 micron to about 15 micron.
- the pigment particle size is in the range from about 0.005 to about 5 micron and, most typically, from about 0.005 to about 1 micron.
- the average particle size as measured by dynamic light scattering is less than about 500 nm, typically less than about 300 nm.
- the selected pigment(s) may be used in dry or wet form.
- pigments are usually manufactured in aqueous media and the resulting pigment is obtained as water-wet presscake.
- presscake form the pigment is not agglomerated to the extent that it is in dry form.
- pigments in water-wet presscake form do not require as much
- pigments with coloristic properties useful in ink jet inks include: (cyan) Pigment Blue 15:3 and Pigment Blue 15:4; (magenta) Pigment Red 122 and Pigment Red 202; (yellow) Pigment Yellow 14, Pigment Yellow 74, Pigment Yellow 95, Pigment Yellow 110, Pigment Yellow 114, Pigment Yellow 128 and Pigment Yellow 155; (red) Pigment Orange 5, Pigment Orange 34, Pigment Orange 43, Pigment Orange 62, Pigment Red 17, Pigment Red 49:2, Pigment Red 112, Pigment Red 149, Pigment Red 177, Pigment Red 178, Pigment Red 188, Pigment Red 255 and Pigment Red 264; (green) Pigment Green 1 , Pigment Green 2, Pigment Green 7 and Pigment Green 36; (blue) Pigment Blue 60, Pigment Violet 3, Pigment Violet 19, Pigment Violet 23, Pigment Violet 32, Pigment Violet 36 and Pigment Violet 38; and (black) carbon black. Colorants are referred to herein by their "C.I.” designation established by Society
- the ink jet ink may contain up to approximately 30% pigment by weight, typically about 0.1 to about 25% pigment by weight, and more typically about 0.25 to about 10% pigment by weight, based on the total ink weight. If an inorganic pigment is selected, the ink will tend to contain higher weight percentages of pigment than with comparable inks employing organic pigment, and may be as high as about 75% in some cases, since inorganic pigments generally have higher specific gravities than organic pigments.
- the function of the polymeric dispersant is to disperse the solid particle, more typically a colorant, in the aqueous vehicle.
- the polymeric dispersant is an AB block copolymer with crosslinkable functional moieties that are crosslinked with crosslinking agents selected from the group consisting of epoxide, carbodiimide, oxazoline, isocyanate, and silane.
- crosslinking agents selected from the group consisting of epoxide, carbodiimide, oxazoline, isocyanate, and silane.
- These block copolymers may comprise an A block that is soluble in the ink vehicle components such as glycols and butyl carbitol, and a B block comprising a random segment of ionic/ potentially ionic and hydrophobic monomers.
- ionic a monomer which may be neutralized to become ionic such as methacrylic acid (MAA).
- MAA may be neutralized with KOH to become an ionic monomer unit.
- the number of units in the A block can be about 5 to about 18, more typically about 6 to about 12, still more typically about 8 to about 12, and most typically about 8 units.
- the number of units in the B block can be about 15 units to about 80 units, more typically about 25 units to about 70 units and most typically about 30 units to about 50 units.
- the B block provides ionic stabilization whereas the A block provides steric stabilization in the ink vehicle.
- Pigments are insoluble particles in the ink vehicle and must be treated in order to form a stable dispersion.
- the pigments are first dispersed in the aqueous vehicle by a block copolymer dispersant having two blocks (or segments), an A block and a B block.
- the A block is an ink vehicle soluble segment of the polymer which provides some steric stabilization in the ink vehicle while also enhancing the surface-activity of the dispersant.
- the B block is a random segment comprising
- the overall polymeric dispersant has a number average molecular weight (Mn) of about 2,000 to about 20,000 Daltons, more typically about 4,000 to about 12,000 Daltons, and an acid number of about 40 to about 220 (mg KOH/g polymer solids) more typically about 50 to about 150 (mg KOH/g polymer solids) .
- the weight ratio of pigment to dispersion (P/D) is typically between about 0.5 and 5.
- a crosslinking compound is then mixed with the dispersion.
- the polymeric dispersant with crosslinkable moiety undergoes a crosslinking reaction and forms a crosslinked network to entrap the pigment suspended in aqueous vehicle; wherein the aqueous dispersion has a pH of at least about 8.0.
- the print properties of the inks are especially enhanced in the presence of metal salts, for example calcium carbonate/-chloride treated papers (ColorLok) and underprinting with salt latent inks such as magnesium nitrate cyan inks.
- metal salts for example calcium carbonate/-chloride treated papers (ColorLok) and underprinting with salt latent inks such as magnesium nitrate cyan inks.
- a Block Composition :
- the function of the A Block is to provide steric stabilization in the ink vehicle leading to stability of the dispersion in the presence of organic components which can be in the ink vehicle that is also known as the aqueous carrier medium.
- organic components often contribute to flocculation of aqueous pigment dispersions.
- the A block of an AB diblock dispersant has good solubility in the organic components, resistance to flocculation can be markedly improved through the extension of the A block out from the pigment surface in the ink vehicle leading to entropic repulsion / steric stabilization.
- typical A block monomers can be non-ionic, hydrophilic and increase surface-activity of the dispersant.
- the constituent monomer(s) of the A block can be hydrophilic or hydrophobic depending on the properties of the organic components, and they may include monomers which are constituents of the B block.
- Structural similarity between the A block and the organic components in the ink vehicle will generally result in good compatibility and steric stabilization.
- the A block comprises at least 50% by weight of a monomer, having the following structure:
- R and Ri are H, or methyl
- R 2 is alkyl of 1 -4 carbon atoms or phenyl
- n is about 1 to about 20, more typically about 1 to about 10.
- the polymers can be just hydrophilic but water insoluble to completely water soluble.
- the solubility of the polymer increases as the number of oxyethylene units increases.
- Typical monomers for the A block can be ethoxy triethylene glycol methacrylate, n-butoxyethyl methacrylate and mixtures thereof.
- the A block can also function to improve polymer properties even in the absence of organic cosolvents It has been found that n-butoxyethyl methacrylate has good compatibility with butyl cellosolve or butyl carbitol, and ethoxy triethylene glycol methacrylate has good compatibility with glycols such as ethylene glycol, diethylene glycol, and tripropylene glycol. In addition, propoxylated methacrylates are soluble in propylene glycols whereas poly(ethoxy- triethylene glycol) methacrylate has good compatibility with poly(ethylene oxide) as well as water.
- the A block can also contain other monomers that may or may not have crosslinkable moieties, that are present in amounts of less than 50 % by weight, and that can be similar to constituents of the B block.
- Examples of other monomers that can be incorporated in the A block include hydroxyethyl methacrylate, methyl methacrylate, methacrylic acid, butyl methacrylate, and 2-dimethylaminoethyl methacrylate. These monomers can be advantageously used in the A block to have
- crosslinkable functional moieties for further crosslinking or to adjust the physical properties, e.g., Tg, of the polymeric dispersant of this disclosure while maintaining the compatibility with an aqueous dispersion system.
- the A block should have minimal interaction with the pigment, and thus, strongly anchoring monomer units, such as styrene, substituted styrene benzyl methacrylate, phenoxyethyl acrylate, are not desirable.
- the B block of the AB block copolymer dispersant comprises ionic/potentially ionic monomers and hydrophobic monomers.
- the ratio of the ionic/potentially ionic monomers and hydrophobic monomer can be about 15 to about 80, more typically about 25 to about 70, and most typically about 30 to about 50.
- each of R 3 -R 5 can be selected from the group consisting of H and CH 3 .
- R 3 and R 4 can be H, and R 5 can independently be selected from H and CH 3 .
- X is selected from the group consisting of:
- R 6 is selected from the group consisting of an alkyl, aryl and alkylaryl group containing 1 -20 carbon atoms, which group may further contain one or more heteroatoms such as O, N, P, S, Si; and
- each of R 7 and R 8 is independently selected from the group consisting of H and an alkyl, aryl and alkylaryl group containing 1-20 carbon atoms, which group may further contain one or more heteroatoms such as O, N, P, S, Si.
- Typical hydrophobic monomers in general include, for example, benzyl methacrylate, butyl methacrylate, methyl methacrylate, ethyl methacrylate, propyl methacrylate, hexyl methacrylate, 2-ethylhexyl methacrylate, octyl methacrylate, lauryl ethacrylate, stearyl methacrylate, phenyl methacrylate, phenoxyethyl methacrylate, methacrylonitrile, glycidyl methacrylate, p-tolyl methacrylate, sorbyl methacrylate, methyl acrylate, ethyl acrylate, propyl acrylate, butyl acrylate, hexyl acrylate, 2- ethylhexyl acrylate, octyl acrylate, lauryl acrylate, stearyl acrylate, phenyl acrylate,
- each of Rg - Rn is selected from the group consisting of H and CH 3 .
- R 9 and Ri 0 is H, and Rn is independently selected from H and CH 3 .
- the Z group can be anionic, cationic, amphoteric or zwittehonic.
- Z group examples include anionic groups selected from the group consisting of sulfonates, sulfate, sulfosuccinate, carboxylate, and phosphate; cationic groups such as amine salts, including quaternary amine salts; amphoteric groups; and zwittehonic groups selected from the group consisting of betaine, +N-C-CO2-, and lecithin.
- the hydrophilic monomers may have single Z substituents or
- the Z group is present as its hydrogen substituted form or as a salt.
- Typical ionic monomers include, for example, methacrylic acid, acrylic acid, maleic acid, maleic acid monoester, itaconic acid, itaconic acid monoester, crotonic acid, crotonic acid monoester, N 1 N- dimethylaminoethyl methacrylate, N,N-diethylaminoethyl methacrylate,
- N-vinyl pyrridine N-vinyl pyrridine, and 2-acrylamido-2-propane sulfonic acid.
- polymerization methods include but are not limited to free radical processes, Group Transfer Processes (GTP), radical addition fragmentation (RAFT), atom transfer reaction (ATR), and the like.
- GTP Group Transfer Processes
- RAFT radical addition fragmentation
- ATR atom transfer reaction
- the overall polymeric dispersant can have a number average molecular weight (Mn) of about 2,000 to about 20,000 Daltons, more typically about 4,000 to about 12,000 Daltons, and an acid number of about 40 to about 220 (mg KOH/g polymer solids), more typically of about
- the weight ratio of pigment to dispersion can be typically between about 0.5 and about 5.
- the crosslinked polymeric dispersant can be typically present in the amount of about 0.1 to about 20% by weight, more typically in the range of about 0.2 to about 10 % by weight, and still more typically in the range of about 0.25% to about 5% by weight, based on the total weight of the ink jet ink.
- Crosslinked Polymeric Dispersant can be typically present in the amount of about 0.1 to about 20% by weight, more typically in the range of about 0.2 to about 10 % by weight, and still more typically in the range of about 0.25% to about 5% by weight, based on the total weight of the ink jet ink.
- polymeric dispersants can have crosslinkable functional moieties which may be in the A block or B block.
- the dispersant is thus capable of crosslinking to a crosslinking compound that has crosslinking functionality reactive with crosslinkable moieties.
- Table 1 identifies suitable functional groups that may be incorporated into the A block or B block of the polymeric dispersant and the companion
- crosslinking groups that may be present in the crosslinking compound.
- the functional moieties can be incorporated into the A block or B block of the polymeric dispersant by selection of appropriate monomers. Mixtures of these crosslinking moieties may also be present in the polymeric dispersant. A separate crosslinking compound having the appropriate group can be added to the dispersion to crosslink the polymeric dispersant.
- Useful crosslinking compounds are those which are soluble or insoluble in the aqueous vehicle, including m- tetramethylxylene diiscyanate (TMXDI), isophorone diisocyanate (IPDI), trimethylopropane polyglycidyl ether, polyglycerol polyglycidyl ether, oxazoline-functional polymers, waterborne polycarbodiimide resin, and silane.
- pH of the crosslinked dispersion can be adjusted to at least about 8.0, more typically about 8.0 to 12.0, and most typically about 8.0 to about 11.0.
- the dispersions of the present disclosure may be prepared using any conventional milling process known in the art. Most milling processes use a two-step process involving a first mixing step followed by a second grinding step. The first step comprises the mixing of all the ingredients, i.e., particle, dispersant(s), liquid carrier(s), pH adjuster and any optional additives, to provide a blended "premix". Typically all liquid ingredients are added first, followed by the dispersant(s) and lastly the solid particle.
- HSD Dispersers,
- the second step comprises milling of the premix to produce a stable dispersion.
- a typical milling process for carbon black pigments that avoids media contamination is the Microfluidizer Process, although other milling techniques can be used.
- a labscale model M-110Y High Pressure Pneumatic, Microfluidizer with a diamond Z- Chamber from Microfluidics of Newton, Massachusetts can be used.
- the Microfluidizer uses an impingement process at high pressures to deaggomerate and mill fine particles, such as pigments.
- the model M- 110Y Microfluidizer can operate at pressure ranges of about 3,000 to about 23,000 psi, although pressures of about 10,000 to about 15,000 are typical.
- the flow rates through the microfluidizer were typically about 200 to about 500 ml/min. and more typically about 300 to about 450 ml/min.
- the milling can be done using a staged procedure in which a fraction of the solvent may be held out of the grind and added after milling is completed. This amount of solvent held out during milling can vary by dispersion and is typically about 100 to about 300 grams of the total 600 gram batch size. This can be done to achieve optimal rheology and viscosity for grinding efficiency. Each dispersion can be processed for a total of 10 passes through the mill although the endpoint can be achieved in less milling time.
- a catalyst can be those that are either soluble or insoluble in the liquid and can be selected depending upon the crosslinking reactions.
- Some suitable catalysts include dibutyltin dilaurate (DBTDL), tributyl amine (“TBA”) and dimethyldodecyl amine.
- pH of the crosslinked dispersion can be adjusted to at least about 8.0, more typically about 8.0 to 12.0, and most typically about 8.0 to about 11.0, if needed. Then the dispersion can be filled into a polyethylene container.
- the dispersion can be further processed using conventional filtration procedures known in the art.
- the dispersions can be processed using ultrafiltration techniques to remove co-solvent(s) and other contaminants, ions or impurities from the dispersion.
- Each dispersion can be then tested for pH, conductivity, viscosity and particle size. Dispersion stability is deemed important to demonstrating the utility of the dispersing resins. Dispersion stability testing included measuring pH, conductivity, viscosity and particle size after oven aging of samples for 1 week at 70 0 C and noting if significant change versus initial readings had occurred.
- Pigmented dispersions can be prepared using the pigment identified earlier.
- the premix can be prepared at typically 23% pigment loading and the dispersant level was set at a P/D (pigment/dispersant), most typically at a P/D of 2.5.
- a P/D of 2.5 corresponds to a 40% dispersant level on pigment
- the dispersant resins can be neutralized with either alkali metal hydroxide such as LiOH, KOH, NaOH, or amine to facilitate solubility and dissolution into water.
- the neutralization process can be done either in situ during the premix stage or by pre-neutralizing the resin during the final stage of manufacture.
- the pigment level can be maintained at about 18 % to about 30%, more typically about 23%, and was reduced to about 12 % to about 18%, more typically about 15% during the milling stage by adding deionized water for optimal milling conditions.
- the dispersions can be reduced to about 10% pigment concentration by adding the de-ionized water and then crosslinked with additional crosslinking compound by thorough mixing at room temperature or elevated temperature for several hours .
- the treated dispersion can be filtered through a filter, for example, a 0.3 micron Chipwich filter, available from Pall Trincor of East Falls, NY, to remove any possible contaminants and placed in a 1000 ml polyethylene container.
- the pigmented ink of this disclosure comprises an ink vehicle typically an aqueous ink vehicle, also known as an aqueous carrier medium, the aqueous dispersion and optionally other ingredients.
- an ink vehicle typically an aqueous ink vehicle, also known as an aqueous carrier medium, the aqueous dispersion and optionally other ingredients.
- the ink vehicle is the liquid carrier (or medium) for the aqueous dispersion(s) and optional additives.
- aqueous ink vehicle refers to an ink vehicle comprised of water or a mixture of water and one or more organic, water-soluble vehicle components commonly referred to as co- solvents or humectants. Selection of a suitable mixture depends on requirements of the specific application, such as desired surface tension and viscosity, the selected pigment, drying time of the pigmented ink jet ink, and the type of paper onto which the ink will be printed. Sometimes in the art, when a co-solvent can assist in the penetration and drying of an ink on a printed substrate, it is referred to as a penetrant.
- water-soluble organic solvents and humectants include: alcohols, ketones, keto-alcohols, ethers and others, such as thiodiglycol, sulfolane, 2-pyrrolidone, 1 ,3- dimethyl-2-imidazolidinone and caprolactam; glycols such as ethylene glycol, diethylene glycol, thethylene glycol, tetraethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, trimethylene glycol, butylene glycol and hexylene glycol; addition polymers of oxyethylene or oxypropylene such as polyethylene glycol, polypropylene glycol and the like; triols such as glycerol and 1 ,2,6-hexanethol; lower alkyl ethers of polyhydric alcohols, such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl, diethylene glycol monoethyl
- the ink vehicle usually contains from about 30% water/ about 70% diethylene glycol to about 95% water/ about 5% diethylene glycol. The more typical ratios are about 60% water/ about 40% diethylene glycol to about 95% water/ about 5% diethylene glycol.
- Percentages are based on the total weight of the ink vehicle.
- a mixture of water and butyl carbitol is also an effective ink vehicle.
- the amount of ink vehicle in the ink is typically in the range of about 70% to about 99.8%, and more typically about 80% to about 99.8%, based on total weight of the ink.
- the ink vehicle can be made to be fast penetrating (rapid drying) by including surfactants or penetrating agents such as glycol ethers and 1 ,2- alkanediols.
- Glycol ethers include ethylene glycol monobutyl ether, diethylene glycol mono-n-propyl ether, ethylene glycol mono-iso-propyl ether, diethylene glycol mono-iso-propyl ether, ethylene glycol mono-n- butyl ether, ethylene glycol mono-t-butyl ether, diethylene glycol mono-n- butyl ether, thethylene glycol mono-n-butyl ether, diethylene glycol mono-t- butyl ether, 1 -methyl-1 -methoxybutanol, propylene glycol mono-t-butyl ether, propylene glycol mono-n-propyl ether, propylene glycol mono-iso- propyl ether, propylene glycol mono
- 1 ,2-Alkanediols are typical. 1 ,2- C4-6 alkanediols, are more typical, 1 ,2-hexanediol, is most typical.
- Some suitable surfactants include ethoxylated acetylene diols (e.g. Surfynol® series from Air Products), ethoxylated alkyl primary alcohols e.g. Neodol® series from Shell) and alkyl secondary alcohols (e.g. Tergitol® series from Union Carbide) alcohols, sulfosuccinates (e.g. Aerosol® series from Cytec), organosilicones (e.g. Silwet® series from Witco) and fluoro surfactants (e.g. Zonyl® series from DuPont).
- ethoxylated acetylene diols e.g. Surfynol® series from Air Products
- glycol ether(s) and 1 ,2-alkanediol(s) added should be properly determined, but it is typically in the range of from about 1 to about 15% by weight, and more typically about 2 to about 10% by weight, based on the total weight of the ink.
- Surfactants may be used, typically in the amount of about 0.01 to about 5% and typically about 0.2 to about 2%, based on the total weight of the ink.
- Biocides may be used to inhibit growth of microorganisms.
- Pigmented ink jet inks typically have a surface tension in the range of about 20 mN.m “1 to about 70 mN.m “1 , at 25°C. Viscosity can be as high as 30 mPa.s at 25°C, but is typically somewhat lower.
- the ink has physical properties compatible with a wide range of ejecting conditions, materials construction and the shape and size of the nozzle.
- the inks should have excellent storage stability for long periods so as not clog to a significant extent in an ink jet apparatus. Further, the ink should not corrode parts of the ink jet printing device it comes in contact with, and it should be essentially odorless and non-toxic.
- the inks of the disclosure are particularly suited to lower viscosity applications.
- the viscosity (at 25 0 C) of the inks of this disclosure may be less than about 7 mPa.s, or less than about 5 mPa.s, and even, advantageously, less than about 3.5 mPa.s.
- a typical printer will generally comprise at least four differently colored inks such as a cyan, magenta, yellow and black (CMYK) ink.
- Ink sets may further comprise one or more "gamut-expanding" inks, including different colored inks such as an orange ink, a green ink, a violet ink, a red ink and/or a blue ink, and combinations of full strength and light strengths inks such as light cyan and light magenta.
- ink sets may include one or more colorless inks which are printed in combination with the colored inks to enhance properties such as optical density, chroma, durability and/or gloss.
- a method of ink jet printing onto a substrate comprising, in any workable order, the steps of: (a) providing an ink jet printer that is responsive to digital data signals;
- R and Ri are H, or methyl
- R 2 is alkyl of 1 -4 carbon atoms or phenyl
- n is about 1 about 20;
- the B block is a segment comprising an ionic monomer and at least one hydrophobic monomer; and wherein the dispersant comprises a crosslinking moiety; wherein the crosslinking moiety is crosslinked with a crosslinking agent selected from the group consisting of epoxide, carbodiimide, oxazoline, isocyanate, and silane; and wherein the aqueous dispersion has a pH of at least about 8.0; and
- the inks of the present disclosure can be printed with any suitable inkjet printer, including printers equipped with piezo or thermal print heads.
- thermal ink jet print heads are the Hewlett Packard Deskjet, and Canon iPIXMA iP4200, and some examples of piezo print heads are Brother MFC3360C, and Epson Stylus C120.
- Some suitable print heads are disclosed in US Patent 6,161 ,918, US Patent 4,490,728, and US Patent 6,648,463, the disclosures of which are incorporated herein by reference.
- the substrate can be any suitable substrate including plain paper, such as common electrophotographic copier paper; treated paper, such as photo-quality inkjet paper. The present disclosure is particularly advantageous for printing on plain paper.
- Denacol® 321 Trimethylolpropane Polyglycidyl Ether
- Denacol® 920 Polypropylene Glycol Diglycidyl Ether
- Denacol® 512 Polyglycerol Polyglycidyl Ether
- dispersant polymers used to make the dispersions were synthesized by established methods as described, for example, in U.S. patents 5,085,698. and 5,852,075 along with U.S. patent publication US2005/0090599, the disclosures of which are incorporated by reference herein as if fully set forth.
- BzMA//MAA//BzMA 8//10//8 is an ABA triblock polymer with a first A block that is on average 8 BzMA (Benzyl Methacrylate) units long, a B block that is on average 10 MAA (Methacrylic Acid) units long, and a final A block that is on average 8 BZMA units long.
- Standard laboratory techniques for handling water sensitive chemicals were employed for the following examples. For example, glassware was extensively dried before use, monomers were stored over sieves, and cannulation procedures were used to keep material dry.
- GPC Gel Permeation Chromatography or GPC was used to verify predicted molecular weight and molecular weight distribution.
- the GPC system included a Waters 1515 lsocratic HPLC Pump, Waters 2414 Refractive Index Detector, 717 plus Waters Autosampler, Four Styregel Columns (HR 0.5, HR 1 , HR 2, and HR 4) in series in a Waters Column Heater set to 4O 0 C. Samples were eluted with Tetrahydrofuran (THF) at a flow rate of 1 mL/min. The samples were analyzed using Breeze 3.30 Software with a calibration curve developed from narrow molecular weight, polymethylmethacrylate (PMMA) standards. Based on light scattering data from Polymer Laboratories Ltd., the nominal, peak molecular weight for the PMMA standards were as follows: 300000, 150000, 60000, 30000, 13000, 6000, 2000, and 1000.
- the particle size was determined by dynamic light scattering using a Microtrac Analyzer, Largo Florida. For many of the dispersion steps, a Model 100 F or Y, Microfluidics System was used (Newton MA).
- the polymeric dispersants are summarized in the table below. Details include dispersant # from cross-referencing with ink and pigment dispersion data, polymer structure in terms of DP or chain length for each monomer unit, architecture (diblock vs random), theoretical number average molecular weight (Mn), and theoretical acid number (mg KOH/g solids). The measured acid number and Mn by GPC are included in the polymer preparation. Note, the polymer composition may also be expressed in terms of weight % for each monomer component. However, in an effort to facilitate comparison between random and block copolymer, these polymer structure are represented in the detailed fashion of monomer unit DP.
- Dispersant 1 Diblock 8ETEGMA//30BzMA/11 MAA
- Dispersant 2 Diblock 8ETEGMA//30BMA/11 MAA
- the ETEGMA conversion was greater than 98% 90 min after the feed was complete. 322.6 g of methanol were added, and then the THF and other volatile by-products were distillated by slowly heating to 12O 0 C while adding 2-pyrrolidone (2P). The final polymer solution was 45.1 % solids with a measured number of 98.2 mg KOH/gram of polymer solids. The molecular weight of this polymer as measured by GPC was Mn 9018, Mw 9635, and PD 1.07. Dispersant 3: Diblock 8ETEGMA//49BzMA/20MAA
- Comparative Dispersant 1 Random 22BzMA/11 MAA
- a 5-liter round bottom flask was dried with a heat gun under nitrogen purge and equipped with a mechanical stirrer, thermocouple, N 2 inlet, drying tube outlet, and addition funnels.
- Tetrahydrofuran (THF) 902 g, was cannulated to the flask.
- Initiator (1 ,1-bis(thmethylsilyloxy)-2-methyl propene, 55 g (0.233 moles)
- catalyst tetrabutyl ammonium m-chlorobenzoate, 0.6 ml of a 1.0 M solution in acetonithle).
- Catalyst solution (tetrabutyl ammonium m-chlorobenzoate, 0.6 ml of a 1.0 M solution in acetonitrile and THF, 29.0 g) was syringe pumped during both the monomer feeds.
- Monomer feed 1 trimethylsilyl methacrylate 412 g (2.59 mol) and Benzyl methacrylate, 918 g (6.46 mol) was added over 45 minutes while the reaction exo-thermed to 65 0 C. After a 1 hr hold, HPLC indicated greater than 98% monomer conversion, then 182.07 g of methanol were added.
- the carbon black pigmented dispersions were prepared using Degussa's Nipex® 180 IQ carbon black pigment. Each carbon black premix was prepared at 23% pigment loading and the amount of dispersant was set at a P/D (pigment/dispersant) of 2.0 that corresponded to a 50% level of active dispersant on pigment. Neutralization of the dispersants was done using a 45.6% active KOH solution.
- Pigment Dispersion 1 was prepared using a two step process in which the dispersion ingredients were added to a 1 Liter stainless steel pot in the order shown below.
- the premix step used a High Shear Disperser, HSD, with a 60 mm Cowels blade operated at 3500 rpm which ran for 2 hours.
- the pigment dispersion milling was performed using a labscale model M-110Y High Pressure Pneumatic, Microfluidizer with a diamond Z- Chamber available from Microfluidics, a division of Microfluidics
- Pigment Dispersion 1 was processed at a pressure of 15,000 psi for a total of 12 passes through the Microfluidizer.
- Step 1 Premix
- a 2200 gram dispersion sample was prepared by adding the following ingredients, in the order listed below, to a 1 Liter stainless steel pot. Each ingredient was added slowly with mixing using an HSD, High Shear Disperser, equipped with a 60 mm Cowels blade and operated at roughly 1000 rpm during ingredient loading. The pigment loading in the premix step was 23%.
- Dispersant 1 BzMA/MAA//ETEGMA 30/11 //8 ) 340.56 KOH Solution (45.6% Active ) 23.2
- Nipex® 180 carbon black pigment 330 Nipex® 180 carbon black pigment 330.
- the premix prepared in Step 1 was milled using a labscale model M-11OY High Pressure Pneumatic, Microfluidizer, with a diamond Z- Chamber from Microfluidics, Newton, Massachusetts.
- the dispersion was milled for a total of 12 passes at a flow-rate of 440 ml/min and pressure of 15,000 psi. After milling was completed at 15% pigment, the dispersion was filtered through a 0.3 micron Chipwich filter available from Pall Trincor, East Falls, NY and collected into a 3000 ml polyethylene container.
- the final pigment dispersion batch size totaled 2200 grams.
- Pigment Dispersion 2 was made using a media milling process and a lab-scale Eiger Minimill, model M250, VSE EXP from Eiger Machinery Inc. Chicago, Illinois.
- the first step comprised the mixing of all the ingredients, that is, pigment, dispersants, KOH, pH adjuster, to provide a blended "premix". All liquid ingredients were added first, followed by the KOH solution which was used to neutralize "in situ" the dispersant and lastly the pigment. Mixing was done in a stirred 10 Liter stainless steel mixing vessel using a high-speed disperser, (HSD), with a 60 mm Cowels type blade attached to the HSD operated at 3500 rpm for a total mixing time of 2 hrs.
- HSD high-speed disperser
- the pigment loading in the premix step was 25%.
- Dispersant 2 (BMA/MAA//ETEGMA 30/11 //8 ) 936.50
- Pigment Red 122 (Sun chemical) 1610.00 After premixing for 2 hrs. at 3500 rpm using the HSD, additional Dl water was added to reduce pigment loading to 23% which gave the desired rheology and was the level used during the media milling stage.
- the media milling or grinding step was performed by charging 820 grams of 0.5 YTZ zirconia media to the mill.
- the dispersion was processed using a re-circulation grinding process with a mill disk speed of 3500 rpm and flow rate of 350 grams per min.
- the milling was done using a staged procedure in which 20% of the Dl water was held out during the grind and added after milling was completed.
- the dispersion was processed for a total of 4 hours milling time.
- Deionized water (final letdown) 1319.3 The pigment dispersion was filtered through a 0.3 micron Chipwich filter available from Pall Trincor of East Falls, NY and collected into a 1000 ml polyethylene container. The final pigment dispersion batch size totaled 5366 grams at 13% pigment loading.
- Pigment Dispersion Comparative Compositions 1 and 2 were prepared by a process similar to the Eiger Minimill process described for Pigment Dispersion 2 with the following exception: Pigment Dispersion Comparative Composition 1 was Pigment Red 122 dispersed with
- Comparative Dispersant 1 (22/11 BzMA/MAA) at a P/D of 2.
- Pigment Dispersion Comparative Composition 2 was Pigment Red 122 dispersed with Comparative Dispersant 2 (13//10 BzMA//MAA).
- Pigment Dispersion 3 was prepared by a process similar to the Eiger Minimill process described for Pigment Dispersion 2 with the following exception: Pigment Yellow 74 (Sun Chemical) was dispersed with Dispersant 2 (8ETEGMA//30BMA/11 MAA) at a P/D of 2.0. Pigment Dispersion 4 (Yellow):
- Pigment Dispersion 4 was prepared by a process similar to the Eiger Minimill process described for Pigment Dispersion 2 with the following exception: Pigment Yellow 74 (Sun Chemical)) was dispersed with Dispersant 3 (8ETEGMA//49BzMA/20MAA ) at a P/D of 2.5.
- Dispersant 2 PR122 8.08 111 180 6 8ETEGMA//30BMA/11 MAA
- crosslinking compound was mixed with the above pigment dispersion, and heated at 60°- 8O 0 C, with efficient stirring, for 6 to 8 hours. After crosslinking reaction was finished, pH was adjusted to at least about 8.0 if needed.
- Table 3 summarized the crosslinking recipe for the pigment dispersion crosslinking.
- Table 4 summarized the final crosslinked pigment dispersions physical properties. Since all crosslinked dispersions had pH above 8.0, no pH adjustment step was performed. As shown in Table 4, crosslinking had no negative impact on dispersion particle size and bigs. Table 3
- Inks were prepared by stirring together the pigment dispersion and the vehicle ingredients listed in Table 5. The dispersion was added in an amount that provided 3% pigment solids in the final ink. Ink physical properties including viscosity, pH, particle size (D50) at room temperature were measured. To test ink stability, above physical properties were re- measured after heat aged at 6O 0 C for 7 days. Pigment particle size growth after dispersion was formulated into the ink and particle size growth after heated aging were indications of dispersion instability. Large increase of viscosity after heat aging was also the indication of dispersion instability. Stability of pigment dispersions before and after the crosslinking step was tested. Results were summarized in Table 6.
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Abstract
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WO2011008813A1 (en) | 2009-07-15 | 2011-01-20 | E. I. Du Pont De Nemours And Company | An aqueous ink jet ink comprising a crosslinking pigment dispersion based on diblock polymeric dispersants |
WO2011008820A1 (en) * | 2009-07-15 | 2011-01-20 | E. I. Du Pont De Nemours And Company | Method of printing using ink jet inks comprising a crosslinking pigment dispersion based on diblock polymeric dispersants |
WO2011063374A1 (en) * | 2009-11-23 | 2011-05-26 | E.I. Du Pont De Nemours And Company | Crosslinked pigment dispersion based on structured vinyl polymeric dispersants |
EP2504403A1 (en) * | 2009-11-23 | 2012-10-03 | E. I. du Pont de Nemours and Company | Method of preparing cross-linked colorant dispersions |
JP6302359B2 (en) * | 2013-06-06 | 2018-03-28 | 花王株式会社 | Water-based ink for inkjet recording |
US20150005466A1 (en) * | 2013-07-01 | 2015-01-01 | E I Du Pont De Nemours And Company | Ab block copolymer dispersants having an ink vehicle soluble block |
JP6189183B2 (en) * | 2013-11-12 | 2017-08-30 | 大塚化学株式会社 | Pigment dispersant and pigment dispersion composition containing the same |
GB2528121A (en) * | 2014-07-11 | 2016-01-13 | Fujifilm Imaging Colorants Inc | Printing process |
JP6031586B1 (en) * | 2015-05-08 | 2016-11-24 | 花王株式会社 | Water-based ink |
WO2017096169A1 (en) * | 2015-12-03 | 2017-06-08 | Elmer's Products, Inc. | Oxazoline-based adhesive formulations |
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- 2010-07-14 JP JP2012520737A patent/JP2012533652A/en active Pending
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US8591020B2 (en) | 2013-11-26 |
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